5 Questions You Should Ask Yourself Daily to Achieve Success

Constant improvement is not easy. Whether it is a skill, a positive quality, or a way of life you are looking to cultivate, staying on the positive side of the growth curve takes work.

My entire life, I have been immersed in worlds that have taught me how to continuously seek mastery and reinvent myself. I played hockey for 14 years. I played classical piano for 16 years. I played World of Warcraft as a teenager and became one of the highest ranked players in North America, with a gaming blog that had more daily readers than most professional columnists. I was a straight A student and honors graduate in college (after being a straight C student in high school). I went from being a malnourished kid undiagnosed with Celiac Disease, to being a 170-pound fitness model with 7 percent body fat. I graduated college with a degree in “creative writing” (everyone thought I was crazy and certain I’d be unemployed), and three years later, I am a Top Writer on Quora with over 10,000,000 views on my answers, work published in every single top digital publication, and the editor in chief at a digital agency in Chicago called Idea Booth.

I don’t say the above for any other reason than to preface the five personal questions I ask myself on a daily basis. Through all of my disjointed and in no way related interests, I have somehow found continuity and long-lasting parallels. Each one of my interests (or should I say “obsessions”) has taught me something very different, and yet they are all founded on the same basic principles.

In order to achieve “success” (and I put that word in quotations because success means different things to different people in different contexts), you need to constantly ask yourself these five questions.

1. What Is My Unique Ability?

Every single day, ask yourself, “What is the one thing that only I can do that no one else can?”

This question takes a bit of work. Most people stop at the surface: “Well, I really like to design, but there are plenty of designers out there, so I guess I’m not really all that different.”

What makes you unique isn’t necessary what you do, but rather how you do it — or more importantly, why you do it. Plenty of companies make glasses. Warby Parker succeeds because they make glasses with a purpose. Plenty of companies make computers. Apple makes computers for the creative rebels. Plenty of people know how to do digital marketing, or run Facebook ads, or design something in Photoshop. Very few people know how to start a movement.

Finding your unique ability takes hard work. It takes digging. You have to really look for all the things you are good at, and then find the convergence point where they all come together.

Your unique ability isn’t one strength. It’s the sum of all your strengths.

2. Am I Still Growing?

This is something I learned through my years immersed in the world of competitive fitness — it’s always about growth. Who you were yesterday doesn’t matter. The only thing that matters is if you are growing right now.

In the gym, we lived by the law “It doesn’t count unless it hurts.” Any time I found myself performing exercises easily, I switched up my routine. Any time I didn’t feel like I was exhausted, I pushed myself harder. Any time I didn’t feel like I was growing fast enough, I looked at every single variable (diet, workout, water intake, etc.) and I adjusted accordingly. Because if I wasn’t growing, I felt like I was dying.

Intense, but that’s the truth.

The same can be said for everything in life. The moment you feel comfortable, you need to change things up. The second you feel like, “Hey, I’m starting to get this!” is when you know you need to look for the next challenge. Another favorite quote of mine is, “If you know what you’re doing, you’re not trying hard enough.”

Do whatever it takes to keep yourself in environments and surrounded by people that will force you to grow. When I audit my life, I don’t so much care about how much money I’m making, or how many awards or pats on the back I’m receiving. I care about whether or not I am growing.

If you’re in an environment of growth, soak up everything you can.

If you’re not, get out.

Don’t Every Stop Growing. Photo by Twenty20.

3. Am I Taking Care of Myself?

Contrary to the very “yang” above, an important part of reaching any level of “success” is constantly checking in with yourself — balancing with the “yin.”

A large part of my daily practice is meditation. I start every morning with a short reading from a book that helps ground my thoughts, followed by a 15-minute meditation. Sometime in the afternoon, I try to take 10 or 15 minutes and go outside, clear my head, and prepare for the second half of my day. At night, if I find myself agitated or bothered in any way, I pause, sit somewhere (a restaurant bathroom, even) and center myself. I rarely drink alcohol. I eat extremely healthfully. And I am protective of my time and how I spend it.

I prioritize taking care of myself over just about everything.

The truth is, if you want to be good — really good, like Michael Jordan good — then you need to live your life as if you are an NBA All-Star and you have a game against your biggest rival tomorrow. If that were your life, you wouldn’t do a single thing to keep yourself from playing the best game of your life. That needs to be how you treat every single day.

This isn’t a sprint, it’s a marathon. This isn’t about some “quick path” to “success.” This is about a way of life that is going to carry you from one success to the next, to the next, to the next.

Take care of yourself. It’s going to be a long road.

4. What Is the Next Skill I Need?

No matter what your pursuit is in life, it’s important that you constantly add new skills to your toolbox.

Every three months, I take a quick look at what I’ve learned over the past three months, and then try to pinpoint what I need to learn over the next three months. For a long time, I thought that every single skill needed to be directly correlated to my primary aim (that thing I wanted to “achieve”), but I’ve learned that’s just not true. The key is to follow your interest and imagination, wherever it may lead. Music has helped my writing, my writing has helped my ability to market and advertise, my ability to market and advertise has helped my communication skills, my communication skills have helped me better discuss my writing, my ability to discuss my writing has helped me teach other writers, etc.

The truth is, you never know when or how a certain skill will prove valuable. But I can say with 100 percent certainty that any skill I have acquired out of genuine interest (I’m not talking about being forced to learn geometry as a high school student) has led me down a good path.

Don’t worry about where it’s going to lead. If you’re interested in it right now, then follow that interest and walk the path to its end. Once you’ve learned what you needed to learn, the path will end, your interest will return to something else, and you’ll be on your merry way.

Don’t overthink it. Trust, and just focus on learning and mastering the skill.

Stay Grounded. Photo by Twenty20.

5. What Am I Most Proud of?

The black hole (and dark side) of all the above is that when you live in a constant state of growth, you begin to lose your bearings. You feel as though you are on a roller coaster, and you are changing and growing so fast, you almost lose perspective on where you ever were in the first place.

It is so, so, so important to pause and enjoy your “successes” along the way. Whether that’s something tangible, like a raise or a new car, or something intangible, like a healthier self-esteem or a newfound sense of confidence, it’s crucial to enjoy those moments. If you don’t, you will feel like a hamster on a wheel, never taking a break, never resting, always looking for the next reward — and then the reward will come and you won’t even realize it because you’re already onto the next task.

It’s a fine line, but it’s necessary for balance. Constant growth is great, but what good is it to reach for the sun if you never stop to enjoy the sun in the first place?

Be like a tree. Always growing, and at the same time, always grounded.